diff --git a/webmail/classes/class_smtp.php b/webmail/classes/class_smtp.php
index 08d67df..c59e137 100644
--- a/webmail/classes/class_smtp.php
+++ b/webmail/classes/class_smtp.php
@@ -14,7 +14,7 @@
  *
  * @package    NOCC
  * @license    http://www.gnu.org/licenses/ GNU General Public License
- * @version    SVN: $Id: class_smtp.php 3093 2023-07-21 17:05:24Z oheil $
+ * @version    SVN: $Id: class_smtp.php 3097 2023-09-05 10:44:26Z oheil $
  */
 
 require_once 'exception.php';
@@ -193,6 +193,39 @@ class smtp {
 		}
 		return (true);
 		break;
+          case 'NTLM':
+		fputs($smtp, "helo " . $_SERVER['SERVER_NAME'] . "\r\n"); 
+		$response="";
+		if( $this->check_response("STARTTLS HELO",$smtp,$response) ) {
+			return new NoccException($html_smtp_error_unexpected . ' : ' . $response); 
+		}
+		fputs($smtp, "AUTH NTLM\r\n"); 
+		$response="";
+		if( $this->check_response("STARTTLS AUTH NTLM",$smtp,$response) ) {
+			return new NoccException($html_smtp_error_unexpected . ' : ' . $response); 
+		}
+
+		$message=NTLM_type1message();
+		fputs($smtp, base64_encode($message)."\r\n"); 
+		$response="";
+		if( $this->check_response("NTLMSSP",$smtp,$response) ) {
+			return new NoccException($html_smtp_error_unexpected . ' : ' . $response); 
+		}
+		$matches=array();
+		if( preg_match("/^NTLMSSP:334\s+(.*)\s+|$/",$response,$matches) ) {
+			$response=$matches[1];
+		}
+		$response=base64_decode($response);
+
+		$message=NTLM_type3message($response,"","",$user, $password);
+		fputs($smtp, base64_encode($message)."\r\n"); 
+		$response="";
+		if( $this->check_response("NTLMSSP",$smtp,$response) ) {
+			return new NoccException($html_smtp_error_unexpected . ' : ' . $response); 
+		}
+
+		return(true);
+		break;
           case 'TLS':
 		fputs($smtp, "STARTTLS\r\n");
 		$response="";
diff --git a/webmail/utils/crypt.php b/webmail/utils/crypt.php
index 3416254..2eae570 100644
--- a/webmail/utils/crypt.php
+++ b/webmail/utils/crypt.php
@@ -14,9 +14,180 @@
  * @package    NOCC
  * @subpackage Utilities
  * @license    http://www.gnu.org/licenses/ GNU General Public License
- * @version    SVN: $Id: crypt.php 3016 2022-08-25 11:00:42Z oheil $
+ * @version    SVN: $Id: crypt.php 3097 2023-09-05 10:44:26Z oheil $
  */
 
+
+/**
+ * Returns NTLM Type 3 message
+ * @param string $type2message the Type 2 message from the server as a binary string
+ * @param string $realm the clients realm/domain (not empty)
+ * @param string $workstation the clients host name (not empty)
+ * @param string $user the SMTP user name
+ * @param string $password the users password
+ * @return string $message the binary string composed NTLM Type 3 message to send to the server
+ */
+function NTLM_type3message($type2message="", $realm="", $workstation="", $user="", $password="") {
+	// https://davenport.sourceforge.net/ntlm.html
+	if( strlen($realm)==0 ) {
+		$realm="unknown";
+	}
+	if( strlen($workstation)==0 ) {
+		$workstation="unknown";
+	}
+	if( strlen($type2message)==0 ) {
+		return "";
+	}
+	
+	$tn_sbuffer=unpack("vlength/vsize/Voffset",substr($type2message,12,8));
+	$flags=substr($type2message,20,4);
+
+	$domain=$realm;
+	if( $flags && 0x0100 ) {  // Flag Target Type Domain (0x00010000) in little endian: 0x00000100
+		$tn_data=substr($type2message,$tn_sbuffer['offset'],$tn_sbuffer['size']);
+		$domain=mb_convert_encoding($tn_data,"ASCII","UCS-2LE");
+	}
+
+	$challenge=substr($type2message,24,8);
+
+	$pw_uni=mb_convert_encoding($password,"UCS-2LE");
+
+	$message="";
+
+	if( extension_loaded("openssl") && function_exists("openssl_encrypt")
+		&& extension_loaded("hash") && function_exists("hash")
+		&& in_array("md4",hash_algos())
+		&& count( preg_grep("/^des-ecb$/i",openssl_get_cipher_methods(true)) ) > 0
+	) {
+		$md4=hash("md4", $pw_uni, false);
+		$md4=hex2bin($md4);
+		$pad=$md4.str_repeat(chr(0),21-strlen($md4));
+
+		$iv_size=openssl_cipher_iv_length("des-ecb");
+		$iv="";
+		for($i=0;$i<21;$i+=7) {
+			$packed="";
+			for($p=$i;$p<$i+7;$p++) {
+				$packed.=str_pad(decbin(ord(substr($pad,$p,1))),8,"0",STR_PAD_LEFT);
+			}
+			$key="";
+			for($p=0;$p<strlen($packed);$p+=7) {
+				$s=substr($packed,$p,7);
+				$b=$s.((substr_count($s,"1") % 2) ? "0" : "1");
+				$key.=chr(bindec($b));
+			}
+			$message.=openssl_encrypt($challenge,"des-ecb",$key,$options=OPENSSL_RAW_DATA|OPENSSL_ZERO_PADDING,$iv);
+		}
+	}
+	else if( extension_loaded("mcrypt") && function_exists("mcrypt_encrypt")
+		&& extension_loaded("hash") && function_exists("hash")
+		&& in_array("md4",hash_algos())
+	) {
+		$md4=hash("md4", $pw_uni, false);
+		$md4=hex2bin($md4);
+		$pad=$md4.str_repeat(chr(0),21-strlen($md4));
+
+		$iv_size=mcrypt_get_iv_size(MCRYPT_DES,MCRYPT_MODE_ECB);
+		$iv=mcrypt_create_iv($iv_size,MCRYPT_RAND);
+		for($i=0;$i<21;$i+=7) {
+			$packed="";
+			for($p=$i;$p<$i+7;$p++) {
+				$packed.=str_pad(decbin(ord(substr($pad,$p,1))),8,"0",STR_PAD_LEFT);
+			}
+			$key="";
+			for($p=0;$p<strlen($packed);$p+=7) {
+				$s=substr($packed,$p,7);
+				$b=$s.((substr_count($s,"1") % 2) ? "0" : "1");
+				$key.=chr(bindec($b));
+			}
+			$message.=mcrypt_encrypt(MCRYPT_DES,$key,$challenge,MCRYPT_MODE_ECB,$iv);
+		}
+	}
+	else {
+		return "";
+	}
+
+	$r_unicode=mb_convert_encoding($domain,"UCS-2LE");
+	$r_length=strlen($r_unicode);
+	$r_offset=64;
+	$u_unicode=mb_convert_encoding($user,"UCS-2LE");
+	$u_length=strlen($u_unicode);
+	$u_offset=$r_offset+$r_length;
+	$ws_unicode=mb_convert_encoding($workstation,"UCS-2LE");
+	$ws_length=strlen($ws_unicode);
+	$ws_offset=$u_offset+$u_length;
+	$lm=mb_convert_encoding("","UCS-2LE");
+	$lm_length=strlen($lm);
+	$lm_offset=$ws_offset+$ws_length;
+	$ntlm=$message;
+	$ntlm_length=strlen($ntlm);
+	$ntlm_offset=$lm_offset+$lm_length;
+	$session="";
+	$session_length=strlen($session);
+	$session_offset=$ntlm_offset+$ntlm_length;
+
+	$message="NTLMSSP\0".
+	"\x03\x00\x00\x00".
+	pack("v",$lm_length).
+	pack("v",$lm_length).
+	pack("V",$lm_offset).
+	pack("v",$ntlm_length).
+	pack("v",$ntlm_length).
+	pack("V",$ntlm_offset).
+	pack("v",$r_length).
+	pack("v",$r_length).
+	pack("V",$r_offset).
+	pack("v",$u_length).
+	pack("v",$u_length).
+	pack("V",$u_offset).
+	pack("v",$ws_length).
+	pack("v",$ws_length).
+	pack("V",$ws_offset).
+	pack("v",$session_length).
+	pack("v",$session_length).
+	pack("V",$session_offset).
+	"\x01\x02\x00\x00".
+	$r_unicode.
+	$u_unicode.
+	$ws_unicode.
+	$lm.
+	$ntlm;
+
+	return $message;
+}
+
+/**
+ * Returns NTLM Type 1 message
+ * @param string $realm the clients realm/domain (not empty)
+ * @param string $workstation the clients host name (not empty)
+ * @return string $message the binary string composed NTLM Type 1 message to send to the server
+ */
+function NTLM_type1message($realm="", $workstation="") {
+	// https://davenport.sourceforge.net/ntlm.html
+	if( strlen($realm)==0 ) {
+		$realm="unknown";
+	}
+	if( strlen($workstation)==0 ) {
+		$workstation="unknown";
+	}
+	$r_length=strlen($realm);
+	$ws_length=strlen($workstation);
+	$ws_offset=32;
+	$r_offset=$ws_offset+$ws_length;
+	$message="NTLMSSP\0".
+		"\x01\x00\x00\x00".
+		"\x07\x32\x00\x00".
+		pack("v",$r_length).
+		pack("v",$r_length).
+		pack("V",$r_offset).
+		pack("v",$ws_length).
+		pack("v",$ws_length).
+		pack("V",$ws_offset).
+		$workstation.
+		$realm;
+	return $message;
+}
+
 function encrXOR($string, $key) {
     for ($i=0; $i<strlen($string); $i++) {
         for ($j=0; $j<strlen($key); $j++) {